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Added 2 hours ago
Staff Data Scientist, Applied ML
Jobber
Remote, Canada
Full-time · Remote
Reporting to the Manager, Data Science, the Staff Data Scientist, Applied Machine Learning will own models and systems for automated decisioning. You will train and evaluate models using…
Added 20 hours ago
Customer Success Manager
SWTCH Energy Inc.
Remote, Canada
Full-time · Remote
…and intelligent for everyone. As a bilingual Customer Success Manager (CSM), you'll play a critical role in helping our customers get the full value of SWTCH's EV charging and energy…
Added 23 hours ago
Head of Fraud Operations (Banking)
Wealthsimple Technologies
Remote, Canada
$155,000 to $175,000 CAD / year
Full-time · Remote
As Head of Fraud Operations (Senior Manager level), you will lead the operational engine safeguarding Wealthsimple and its clients. Overseeing a high-performing, cross-functional…
Added 23 hours ago
Senior Partner Enablement Manager
Docker
Remote, Canada
Full-time · Remote
Docker is looking for a Senior Partner Enablement Manager to own internal and external partner enablement and drive aligned GTM outcomes across our partner ecosystem. Reporting to the Sr.…
Added 1 day ago
Senior Project Manager, Aircraft Program Development (ACP)
Dominion Dynamics
Remote, Canada
Full-time · Remote
…development cost of the ACP aircraft against the baseline set by the Program Manager. Technical decision authority lies with your peers, but you own scope, schedule and…
Added 1 day ago
Growth Marketing Manager
Wagepoint
Remote, Canada
$115,000 to $125,000 CAD / year
Full-time · Remote
We’re looking for a talented Growth Marketing Manager who enjoys tackling hard problems and wants to create meaningful impact for small businesses across Canada. You'll own our SMB…
Added 2 days ago
Retention Specialist
Jobber
Remote, Canada
Full-time · Remote
Reporting to the Manager, Customer Retention, the Retention Specialist works directly with customers who may be at risk of cancelling or disengaging from Jobber. Your job is to understand…
Added 3 days ago
Marketing Operations Manager
Optro
Remote, Canada
$102,000 to $140,000 CAD / year
Full-time · Remote
…fixing what breaks across our connected systems. You'll set the technical standard our execution partners work to, with real autonomy in how you get the work done in a scalable…
Added 3 days ago
Success Operations Analyst I
Thumbtack
Remote, Canada
Full-time · Remote
…frontline work more reliable. We combine analysis with hands-on program delivery, testing changes and scaling what…
Added 3 days ago
Technical Account Manager
Benevity
Remote, Canada
$61,800 to $84,920 CAD / year
Full-time · Remote
Benevity’s Technical Account Manager (TAM) will play a pivotal role in establishing and nurturing strong relationships with our clients. The TAM will be the bridge between the technical…
Added 3 days ago
Technical Account Manager - Term
Benevity
Remote, Canada
Full-time · Remote
Benevity’s Technical Account Manager (TAM) will play a pivotal role in establishing and nurturing strong relationships with our clients. The TAM will be the bridge between the technical…
Added 3 days ago
Technical Account Manager - Term
Benevity
Remote, Canada
$61,800 to $84,920 CAD / year
Full-time · Remote
Benevity’s Technical Account Manager (TAM) will play a pivotal role in establishing and nurturing strong relationships with our clients. The TAM will be the bridge between the technical…
Added 3 days ago
Technical Account Manager
Benevity
Remote, Canada
Full-time · Remote
Benevity’s Technical Account Manager (TAM) will play a pivotal role in establishing and nurturing strong relationships with our clients. The TAM will be the bridge between the technical…
Added 4 days ago
Project Manager, Major Vertical Infrastructure (PFT) (NU 37.26)
Norfolk County
Remote, Canada
Full-time · Remote
As the Project Manager, Major Vertical Infrastructure, you will lead complex water and wastewater infrastructure projects from planning through construction and warranty. You’ll coordinate…
Added 4 days ago
Senior Financial Analyst (PFT) (CUPE 78.26)
Norfolk County
Remote, Canada
Remote
…Association (CPA) or enrolment within three months of hire in the program to achieve a designation within the prescribed policy of the CPA is…
Added 4 days ago
Senior Lifecycle Marketing Manager
Docker
Remote, Canada
Full-time · Remote
Builder's Mindset: You'd rather own a program end to end, strategy, build, QA, and send, than hand pieces of it off. You bring structure to ambiguity: turning a fast-growing list of…
Added 4 days ago
Oracle Cloud Developer
Nuvei
Remote, Canada
Remote
Nuvei is looking for an Oracle Cloud Developer to join the UFS Reimagined program within the Finance organization. The program is delivering Oracle Fusion Cloud ERP and EPM across the Nuvei…
Added 4 days ago
Business Development Manager - Mining
Castolin Eutectic
Remote, Canada
$110,000 to $150,000 CAD / year
Full-time · Remote
Looking for an opportunity where your earning potential is unlimited and your technical expertise makes a real difference?
Added 4 days ago
Senior Website Project Manager
Kanopi
Remote, Canada
Full-time · Remote
As Kanopi continues to grow, we’re excited to welcome a new Senior Website Project Manager to our team.
Added 4 days ago
Organizational Change and Transformation Manager
Pearl Consulting Group
Remote, Canada
Full-time · Remote
The Organizational Change & Transformation Manager will work closely with client executives, program and project managers, technical teams, business leaders, and end users to ensure…
Added 4 days ago
Gestionnaire, Opérations Marketing / Manager, Marketing Operations
Genetec
Remote, Canada
Full-time · Remote
Added 5 days ago
Account Specialist, Growth
1Password
Remote, Canada
Full-time · Remote
…trusted. We innovated the market-leading enterprise password manager and pioneered Unified Access Management, a new cybersecurity category built for the way people and AI agents work today.…
Added 5 days ago
Sr. Product Manager, Mobile App
Rivian and Volkswagen Group Technologies
Remote, Canada
$96,800 to $128,260 CAD / year
Full-time · Remote
We are seeking a Product Manager to help lead the Rivian mobile app experience. The app is how owners live with their vehicle every day: checking status and state of charge, sending remote…
Added 6 days ago
Senior AI Engineer - AI Platform & ML Engineering
Aviso Wealth
Remote, Canada
$135,000 to $150,000 CAD / year
Full-time · Remote
…Machine Learning, Mathematics, Statistics, Engineering or related technical…
Added 6 days ago
Senior Product Manager, Supply
Jobber
Remote, Canada
Full-time · Remote
We’re looking for a Senior Product Manager, Supply to be part of our Ecosystem product organization.

Jobber

Retention Specialist

Remote, Canada

Pay: This role comes with a fixed compensation structure of $58,300.
Job type: Full-time
Workplace: Remote
Posting language: English
Posted: Sep 23, 2026

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Original job description

Are you passionate about helping customers succeed, solving meaningful problems, and making a real impact on the businesses you support every day?

We’re looking for a Retention Specialist to join our Customer Success team and play a key role in helping customers overcome challenges, rediscover the value of Jobber, and continue growing their businesses with confidence.

The Team:

The Retention team plays a critical role in protecting recurring revenue and strengthening long-term customer relationships, supporting customers at pivotal moments when they are deciding whether to continue their Jobber subscription.

Through both inbound and outbound retention conversations, our team connects with customers who may be experiencing challenges, exploring alternatives, or not yet seeing the full value of the platform. We take the time to understand what’s getting in the way, and then connect them to the Jobber features and workflows that solve their specific problems and help their businesses grow.

We partner closely with Customer Success, Support, Product, and Billing to surface churn risks, share insights from customer conversations, and continuously improve the overall customer experience.

The Role:

Reporting to the Manager, Customer Retention, the Retention Specialist works directly with customers who may be at risk of cancelling or disengaging from Jobber. Your job is to understand what’s standing in their way, and connect them to solutions that help them succeed.

You’ll lead meaningful, consultative conversations to understand the underlying causes behind cancellation requests or disengagement, identify barriers to success, and guide customers toward solutions that strengthen their experience with Jobber and make a real difference for their business. You’ll ask the right questions before offering solutions, and you’ll treat every conversation as an opportunity to genuinely improve someone’s experience.

Retention Specialists engage with customers through inbound calls, proactive retention outreach, and scheduled value sessions, translating Jobber’s capabilities into practical, meaningful solutions tailored to each customer’s unique situation.

You’ll develop deep product knowledge and act as a trusted advisor to customers, confidently navigating complex conversations and leveraging your expertise to showcase how Jobber’s features solve meaningful problems for businesses, helping customers make informed decisions that drive their long-term success.

Success in this role is measured through outcomes such as save rate, customer retention, and long-term customer success following retention conversations, with Retention Specialists taking direct ownership of outcomes that impact recurring revenue retention.

Shift: Monday to Friday 11am to 8pm MT (1pm to 10pm ET)

Please note: This role is available only to candidates based in Edmonton, Toronto, Vancouver, or Kitchener-Waterloo and requires you to attend the office at least 1 day per week according to the department schedule

The Retention Specialist will:

Engage with customers at risk of cancellation through retention-focused phone conversations via direct inbound phone line or booked calls, identifying solutions that help them continue to succeed with Jobber.
Conduct proactive outbound retention calls to customers showing signs of churn risk, using available signals such as account health indicators or changes in engagement to help customers address challenges before they lead to cancellation.
Facilitate scheduled value sessions that help customers overcome blockers and unlock the full value of their Jobber subscription through feature adoption, workflow optimization, training, and best practices tailored to their business.
Use a consultative, diagnostic approach to uncover root causes behind churn risk. You’ll ask the right questions, interpret signals such as product usage patterns and account health indicators, and recommend solutions that genuinely address what’s getting in the customer’s way.
Play a direct role in protecting and retaining recurring revenue by influencing customer decisions at critical moments in their lifecycle, guiding at-risk customers toward solutions that reinforce the long-term value of their Jobber subscription.
Exercise sound judgment and decision-making in navigating complex or high-risk customer situations, balancing customer needs with business outcomes to drive the best possible retention result.
Partner with cross-functional teams to share insights from retention conversations, helping identify churn trends, surface product gaps, and contribute to improvements across the customer experience.
Contribute to improving long-term retention strategy by identifying patterns in churn drivers and influencing cross-functional improvements to product, onboarding, and customer experience.
Adapt quickly to evolving processes, tools, and product updates in a growing environment where customer needs and solutions continue to evolve.
Become an ambassador of our culture by being humble, supportive – and someone who truly gives a shit!

To be successful, you should have:

A track record of thriving in high-volume, customer-facing environments where you consistently deliver strong results while maintaining a high-quality customer experience.
A genuine curiosity about what’s driving customer challenges. You ask great questions, listen closely, and understand the problem before proposing a solution.
The ability to translate product knowledge into customer solutions. You don’t just know what Jobber does – you can connect its features to the specific needs of each customer’s business in a way that resonates.
The ability to influence outcomes through consultative conversations, confidently guiding customers through complex situations such as cancellation decisions, product challenges, or pricing concerns.
Strong verbal communication skills and a customer-first mindset, allowing you to build rapport quickly and navigate challenging conversations with empathy and clarity.
A results-driven mindset that motivates you to take ownership of customer outcomes and work toward solutions that support long-term customer success.
Resilience and composure. You stay calm under pressure, handle rejection professionally, and learn quickly from difficult conversations.
Strong problem-solving ability. You assess situations critically, identify root causes, and propose creative, practical solutions with confidence.
Adaptability in a growth environment. You’re energized by change and comfortable learning new tools, systems, and workflows.
Reliability and accountability. You show up for your team and customers, follow through on commitments, and take responsibility for results.
Confidence working with modern software tools and navigating multiple systems in a fast-paced, cloud-based environment.

Interest or experience in leveraging AI tools to enhance productivity and insight generation.

Compensation:
At Jobber, we believe that compensation should be transparent, fair, and supportive of your experience and growth. This role comes with a fixed compensation structure of $58,300.

Base salary is just one part of a total compensation package that will include equity rewards, annual stipends for health and wellness, retirement savings matching, and an extended health package with fully paid premiums for body and mind. Your professional growth matters to us too! You’ll have access to a dedicated talent development program that includes career coaching and opportunities for career development.

If you have any questions about our compensation approach, we encourage open conversations throughout the hiring process!

What you can expect from Jobber:

A total compensation package that includes an extended health benefits package with fully paid premiums for both body and mind, matching in RRSP, TFSA or FHSA, and stock options.
A dedicated Talent Development team and access to coaching, learning, and leadership programs to help you grow your career, reach your goals, and unlock your full potential.
A unique opportunity to build, grow, and leave your impact on a $400-billion industry that has no dominant player...yet.
To work with a group of people who are humble, supportive, and give a sh*t about our customers.

We believe that diverse teams perform better and that fostering an inclusive work environment is a key part of growing a successful team. We welcome people of diverse backgrounds, experiences, and perspectives. We are an equal opportunity employer, and we are committed to working with applicants requesting accommodation at any stage of the hiring process.

A bit more about us:

Job by job, we’re transforming the way service is delivered. Your lawn care provider, home cleaning service, plumber or painter could use Jobber to better connect with their customers, save time in the office, invoice faster, and get paid! We’re bringing tens of thousands of people together with technology to deliver billions of dollars a year in services to happy customers. Jobber exists to help make these small businesses successful, and when they’re successful we all win!

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More about this job

Responsibilities

The Retention Specialist manages at-risk customer accounts through inbound and outbound calls to identify churn drivers and provide tailored solutions. They collaborate with cross-functional teams to share insights and improve the overall customer experience and retention strategy.

Requirements

Candidates should have a proven track record in high-volume, customer-facing roles with strong problem-solving and communication skills. Proficiency in navigating modern software tools and a consultative approach to customer success are essential for this position.

Skills

Customer retention
Consultative selling
Problem solving
Communication
Product knowledge
Relationship management
Data analysis
Conflict resolution
Account management
Customer success
Time management
Adaptability
Active listening
Technical proficiency

Benefits

Extended health benefits
Stock options
Retirement savings matching
Annual stipends for health and wellness
Career coaching
Leadership programs

Visa sponsorship

Not detected in the job text

Keywords

Retention Specialist
Customer Success
Churn Prevention
Recurring Revenue
Consultative Sales
Account Health
Feature Adoption
Workflow Optimization
Customer Experience
SaaS
Cloud-based software
AI tools
Problem Solving
Relationship Building
Data-driven
Customer Retention
Inbound Sales
Outbound Sales
Product Knowledge
Cross-functional Collaboration

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